78277-22-2

Upstream product

• 822-87-7 2-Chlorocyclohexanone 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 100-51-6 benzyl alcohol 
• 287-92-3 Cyclopentane 
• 201230-82-2 carbon monoxide 
• 3400-45-1 cyclopentanecarboxylic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 181235-20-1 1-tert-Butoxycarbonylmethyl-cyclopentanecarboxylic acid benzyl ester 
• 378247-23-5 1-allyl-cyclopentanecarboxylic acid benzyl ester 
• 1376437-23-8 propan-2-yl 3-{[4-(3-{1-[(benzyloxy)carbonyl]cyclopentyl}prop-1-yn-1-yl)phenyl]carbonyl}-2-ethylindolizine-7-carboxylate 
• 1376437-21-6 benzyl 1-(prop-2-yn-1-yl)cyclopentanecarboxylate 
• 378247-24-6 1-carboxymethyl-cyclopentanecarboxylic acid benzyl ester 
• 1376437-29-4 3-{[4-(3-{1-[(tert-butoxycarbonyl) (methyl)amino]cyclopentyl}propyl)phenyl]carbonyl}-2-ethylindolizine-7-carboxylic acid 
• 1376437-26-1 propan-2-yl 3-{[4-(3-{1-[(tert-butoxycarbonyl)amino]cyclopentyl}propyl)phenyl]carbonyl}-2-ethylindolizine-7-carboxylate 
• 1376437-24-9 1-{3-[4-({2-ethyl-7-[(propan-2-yloxy)carbonyl]indolizine-3-yl}carbonyl)phenyl]propyl}cyclopentane carboxylic acid 
• 1257266-84-4 1-(2-oxo-ethyl)-cyclopentanecarboxylic acid benzyl ester 

Relevant academic research and scientific papers

Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols

Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the C sp3 ?H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.

Metal-free radical oxidative alkoxycarbonylation and imidation of alkanes

A metal-free radical oxidative carbonylation of alkanes is demonstrated, yielding esters and imides by means of di-tert-butylperoxide as an oxidant. Various alkanes, alcohols and amides were compatible in this system generating the desired carbonyl products in up to 86% yields. We proposed a plausible radical cross-coupling process based on the preliminary mechanistic studies.

Oxidative Alkane C?H Alkoxycarbonylation

Directly utilizing a chemical feedstock to construct valuable compounds is an attractive prospect in organic synthesis. In particular, the combination of C(sp3)?H activation and oxidative carbonylation involving alkanes and CO gas is a promising and efficient method to synthesize carbonyl derivatives. However, due to the high C?H bond dissociation energy and low polarity of unactivated alkanes, the carbonylation of unactivated C(sp3)?H bonds still remains a great challenge. In this work, we introduce a palladium-catalyzed radical oxidative alkoxycarbonylation of alkanes to prepare numerous alkyl carboxylates. Various alkanes and alcohols were compatible, generating the desired products in up to 94 % yield. Remarkably, ethane, a constituent of natural gas, could be employed as a substrate under the standard reaction conditions. Preliminary mechanistic studies revealed a probable palladium-catalyzed radical process.

Cycloalkyl carboxylic acid ester compound preparation method

The present invention discloses a cycloalkyl formate compound preparation method, wherein in the presence of a palladium salt and a peroxide, a cycloalkane compound and an alcohol compound are dissolved in an organic solvent, the system is replaced by a carbon monoxide atmosphere, a reaction is performed for 16-24 h at a reaction temperature of 90-120 DEG C, and separation and purification are performed to obtain the cycloalkyl formate compound. According to the present invention, the used reactants are cheap and easy to obtain, the reaction conditions are simple, the atom economy is high, and the high-selectivity oxidation carbonylation reaction of the cycloalkane compound and the alcohol compound can be achieved so as to obtain the cycloalkyl formate compound; with the method, the precursor of the widely-used drug dicyclomine having treatment effects on intestines and stomach cramps and irritable bowel syndrome can be simply prepared; and the method has application potential in synthesis of drugs, natural products and the like.

METHOD OF TREATING CONTRAST-INDUCED NEPHROPATHY

The present invention provides the use of a neutral endopeptidase inhibitor, in the manufacture of a medicament for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The invention also relates to the use of a compound of Formula I: wherein R1, R2, R3, R5, X, A3, B1, s and n are defined herein, for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The present invention further provides a combination of pharmacologically active agents for use in the treatment, amelioration and/or prevention of contrast-induced nephropathy.

METHOD OF TREATING CONTRAST-INDUCED NEPHROPATHY

The present invention provides the use of a neutral endopeptidase inhibitor, in the manufacture of a medicament for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The invention also relates to the use of a compound of Formula I: wherein R1, R2, R3, R5, X, A3, B1, s and n are defined herein, for the treatment, amelioration and/or prevention of contrast-induced nephropathy. The present invention further provides a combination of pharmacologically active agents for use in the treatment, amelioration and/or prevention of contrast-induced nephropathy.

SUBSTITUTED AMINOBUTYRIC DERIVATIVES AS NEPRILYSIN INHIBITORS

The present invention provides a compound of formula (I') or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, X and n are defined herein. The invention also relates to a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

Cyclopropanecarboxylic acid esters as potential prodrugs with enhanced hydrolytic stability

Esters of cyclopropanecarboxylic acid demonstrate a substantial increase in stability under both acid- and base-catalyzed hydrolytic conditions. Comparison of the stability of valacyclovir 13 with the cyclopropane analogue 14 shows that at 40 °C and pH 6 the half-life of 14 is >300 h while the value for 13 is 69.7 h. CBS-QB3 calculations on isodesmic reactions for transfer of groups from an alkane to an ester show that a cyclopropyl group provides hyperconjugative stabilization.